Yankees GM Brian Cashman regrets not trading a former infield star

It took Yankees general manager Brian Cashman a considerable amount of time to convince his superiors to part ways with veteran players last summer, but the idea of reassembling the organization entered his brain a couple years ago.

Of course, all that can be realistically discussed are the trades that did happen–that’s common sense. Cashman’s initiative to move Aroldis Chapman was real, as was his case to market Andrew Miller and Carlos Beltran. Those trades can’t be disputed because they came to fruition. But general managers are allowed to play the ‘shoulda coulda woulda’ game, and Cashman recently admitted that he still regrets holding onto a former Yankees star back in 2013.

To Cashman, it was clear two years earlier that the Yankees lacked the farm system capable of producing the pre-arbitration talent all elite teams — regardless of market size — require. Cashman believed the Yankees should dismantle to some degree. As early as the summer of 2014, Cashman was thinking about trading veteran players for younger assets.

“Turning the clock back with Robby Cano, it looked like he was going to stay with us. We pursued an extension with him ,and it wasn’t even close with what he wanted,” Cashman said. “He was, to me, someone we ultimately should have moved at the deadline but didn’t. So he left us as a free agent.”

The Yankees’ situation last summer was similar to what it had been in 2014 when Cashman began broaching the idea of selling off assets last season.

History tells the rest of the story, as Cano eventually signed a 10-year deal with the Seattle Mariners during the 2014 offseason. But if Cashman took a chance–or was the given the nod to sell by the Yankee brass–the rebuild that exists now might not have transpired.